Director, Software Sales - Upper Mid-Market
New
J
JobgetherSaaS, Fintech
CanadaFull-TimeDirector
SalaryBase salary range of approximately $160,000–$180,000 CAD; On-target earnings (OTE) opportunity ranging from approximately $270,000–$300,000 CAD
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Job Details
- Experience
- 7+ years
- Required Skills
- Account ManagementCRMSaaS
Requirements
- 7+ years of experience in fast-paced SaaS, software, or fintech environments.
- 5+ years of experience leading SaaS sales teams with measurable revenue responsibility.
- 3+ years of experience managing upper mid-market or enterprise sales teams.
- Strong experience selling solutions to finance and technology leaders, including CFOs, VPs of Finance, Controllers, CIOs, CTOs, and related stakeholders.
- Proven track record of exceeding sales quotas and delivering consistent revenue growth.
- Experience implementing and coaching teams on structured sales methodologies and best practices.
- Strong understanding of the complete sales lifecycle, from prospecting and discovery through negotiation, closing, and implementation.
- Experience leading distributed teams across multiple functions and geographic regions.
- Ability to establish operational rigor through metrics, forecasting, pipeline management, and performance analysis.
- Comfortable using CRM platforms, sales analytics, and reporting tools to drive decision-making.
Responsibilities
- Lead, mentor, and develop a team of Software Account Executives responsible for closing complex, multi-stakeholder opportunities.
- Own the annual revenue target for the upper mid-market segment and develop strategies to achieve and exceed sales objectives.
- Build and execute scalable sales processes, methodologies, and operating frameworks to improve team performance.
- Coach sales representatives through discovery, solution selling, ROI discussions, negotiations, closing strategies, and customer handoffs.
- Serve as an executive point of contact for strategic prospects, supporting complex sales cycles and escalations.
- Collaborate with Sales Development, Partner Sales, Marketing, Product, Sales Engineering, Finance, and Implementation teams to maximize growth opportunities.
- Monitor pipeline generation, conversion rates, forecasting accuracy, and overall sales execution.
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